Water → (R)-2-(8-methoxy-1H-benz[g]indol-1-yl)-1-methyl-ethylamine fumarate

HRID 264458Notes

Reaction equation

HRID 264458 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]2=[CH:7][CH:8]=[C:9]3[C:13]([N:12]([CH2:14][C@H:15]([NH:17]C(=O)C(F)(F)F)[CH3:16])[CH:11]=[CH:10]3)=[C:5]2[CH:4]=1.[OH-:26].[K+].[OH2:28].[OH-:29].[Na+]>CO>[C:3]([OH:2])(=[O:29])/[CH:25]=[CH:24]/[C:6]([OH:28])=[O:26].[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]2=[CH:7][CH:8]=[C:9]3[C:13]([N:12]([CH2:14][C@H:15]([NH2:17])[CH3:16])[CH:11]=[CH:10]3)=[C:5]2[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 54398429(R)-N-[2-(8-methoxy-1H-benz[g]indol-1-yl)-1-methyl-ethyl]-trifluoroacetamide

Product 1

HCID 67713972(R)-2-(8-methoxy-1H-benz[g]indol-1-yl)-1-methyl-ethylamine fumarateYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.97 g of (R)-N-[2-(8-methoxy-1H-benz[g]indol-1-yl)-1-methyl-ethyl]-trifluoroacetamide, 1 g of potassium hydroxide, 2 ml of water and 40 ml of methanol was boiled under reflux for 15 hours. The reaction mixture was subsequently poured into 80 ml of 1N sodium hydroxide solution, extracted twice with 80 ml of diethyl ether each time and once with 80 ml of ethyl acetate and the combined organic phases were washed once with 120 ml and dried over magnesium sulfate. After concentration in a vacuum, the residue was dissolved in 100 ml of anhydrous diethyl ether, filtered and treated while stirring with a solution of 322 mg of fumaric acid in 30 ml of methanol. The mixture was stirred at room temperature for 3 hours and the white crystals were subsequently filtered off. 600 mg (69%) of (R)-2-(8-methoxy-1H-benz[g]indol-1-yl)-1-methyl-ethylamine fumarate (1:0.5) with m.p. 209° were obtained.

Workup

  1. temperatureunder reflux for 15 hours
  2. extractionextracted twice with 80 ml of diethyl ether each time
  3. washonce with 80 ml of ethyl acetate and the combined organic phases were washed once with 120 ml
  4. dry with materialdried over magnesium sulfate
  5. concentrationAfter concentration in a vacuum
  6. dissolutionthe residue was dissolved in 100 ml of anhydrous diethyl ether
  7. filtrationfiltered
  8. additiontreated
  9. stirringThe mixture was stirred at room temperature for 3 hours
  10. filtrationthe white crystals were subsequently filtered off

Sources & evidence

ORD record
ord-21ec4f99497f4fec85108b0a6ca34284
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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